Windsor Vacation Packages

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Top Holiday Package Deals in Windsor

Price found within the past 48 hours. Click for updated prices.
Ellipse Executive Apartments

Ellipse Executive Apartments

5 out of 5
Midrand
per person
Oct 17 - Oct 21
found 3 hours ago
Roundtrip flight included
Edmonton (YEG) to Johannesburg (JNB)
9.6/10 Exceptional! (11 reviews)
I liked the hygiene, the fast wi-fi and the two TVs, the only complaint is i did not have a heater in my room

Reviewed on Jun. 27, 2023

Hyde Johannesburg Rosebank

Hyde Johannesburg Rosebank

4 out of 5
Rosebank
per person
Oct 17 - Oct 21
found 3 hours ago
Roundtrip flight included
Edmonton (YEG) to Johannesburg (JNB)
9.6/10 Exceptional! (129 reviews)
Beautiful design, spacious rooms, excellent breakfast and very friendly staff!

Reviewed on Jul. 19, 2025

Melrose Place Boutique Hotel

Melrose Place Boutique Hotel

3.5 out of 5
Sandton
per person
Oct 17 - Oct 21
found 3 hours ago
Roundtrip flight included
Edmonton (YEG) to Johannesburg (JNB)
9.2/10 Wonderful! (40 reviews)
Excellent place, homely atmosphere, pleasant Staff and cooperative administration. What more could you want?

Reviewed on Feb. 22, 2023

Radisson Hotel and Convention Centre OR Tambo Airport

Radisson Hotel and Convention Centre OR Tambo Airport

4.5 out of 5
per person
Oct 17 - Oct 21
found 3 hours ago
Roundtrip flight included
Edmonton (YEG) to Johannesburg (JNB)
8.6/10 Excellent! (343 reviews)
Travelers should be aware that the shuttle runs on every half passed from the airport and not on the hour as communicated by hotel. While the facilities are adequate the Sky bar outside area needs a lot of TL - Painting, dangerous empty voids where plants were are not great next to a 5 story drop. Plane to stay at the hotel as the surrounding area is not safe or inviting.

Reviewed on Aug. 1, 2025

@Sandton Hotel

@Sandton Hotel

3 out of 5
Sandton
per person
Oct 17 - Oct 21
found 3 hours ago
Roundtrip flight included
Edmonton (YEG) to Johannesburg (JNB)
9.2/10 Wonderful! (236 reviews)
The property was has many amenities. However it would be nice to have known about these amenities without happening upon them unexpectedly. Otherwise it was a wonderful stay!

Reviewed on Aug. 5, 2025

Where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
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Sandton

4 out of top 10 points of interest in this area

A noteworthy feature of Sandton is its popular shops. While you're in town, be sure to stop and check out Nelson Mandela Square and Sandton City Mall.

Find hotels in Sandton

Windsor Hotel Deals

City Lodge Hotel at OR Tambo International Airport

City Lodge Hotel at OR Tambo International Airport

3 out of 5
Above Multi-Storey Parkade 2, Level 5, OR Tambo International Airport, Kempton Park, Gauteng
The price is CA $154 per night from Sep 7 to Sep 8
CA $154
CA $181 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (1,706 reviews)
"My husband and I always stay at a city lodge because we know what to expect and it’s comfortable. This time I was really needing assistance with the bage and was not able to reach anyone from the front desk. Other than that it was a great stay"

Reviewed on Aug. 3, 2025

City Lodge Hotel at OR Tambo International Airport
Premier Hotel OR Tambo

Premier Hotel OR Tambo

4 out of 5
73 Gladiator Street, Rhodesfield, Kempton Park, Gauteng
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Aug 16 to Aug 17
CA $114
CA $131 total
Aug 16 - Aug 17
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"This Hotel is what i expected. It has everything and the price excellent"

Reviewed on Aug. 3, 2025

Premier Hotel OR Tambo
@Sandton Hotel

@Sandton Hotel

3 out of 5
5 Benmore Rd, Sandton, Gauteng
Fully refundableReserve now, pay when you stay
The price is CA $97 per night from Sep 7 to Sep 8
CA $97
CA $113 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (237 reviews)
"Super comfortable."

Reviewed on Aug. 4, 2025

@Sandton Hotel
See all 2,389 properties in Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

How much does a Windsor vacation package cost?
Browse and book everything in one place with our Windsor vacation packages, which start from just CA $2,027. Select the hotels and flights that match your travel plans. Then, add on a few tours or experiences for an incredible getaway.
How do I get a cheap travel package to Windsor?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you dollars too. A Windsor vacation package makes it a cinch to arrange the ideal trip. With more than 550 airlines around the world to select from, finding flights that suit your schedule will be no sweat. Not only that, we have over 1,000,000 hotels globally to pick from. Now that's what we call choice. Whatever your budget, Expedia can show you the world.
Where should I stay in Windsor?
Stay where the action happens. Many travelers book hotels within easy reach of top attractions, such as Cresta Shopping Centre, Randpark Golf Club and Johannesburg Eye Hospital.
What are the top hotels in Windsor?
Get your trip off to a fantastic start by reserving a room at Isabel's Guesthouse. It's one of most sought-after hotels in Windsor. Another welcoming option is Khamanzi Lodge And Tours.
How far in advance should I book my Windsor vacation?
Search Expedia to compare international flights as soon as you've got your travel dates. In many cases, you can purchase a seat up to 12 months before departure. If you can't find your preferred carrier, or you've left things to the last minute, don't stress. The lowest prices to Windsor sometimes occur just weeks before departure.
What does an Expedia Windsor travel package include?
From airfares and hotels to car rentals, Expedia can help you create a Windsor package that's right for you. Heading away for a while? Look into a rental car, flight and hotel bundle. If your break is short, a hotel and airfare deal could be what you're after. Tours and activities can be added once you've made your booking. Our vacation packages make it a cinch to save and plan.
What should I know before booking a Windsor travel package?
You can save a tidy sum by combining your hotels, airfares and rental cars. Once you've created your package, you can add on things like activities or sightseeing tours. Your next unforgettable vacation is only a couple of clicks away.
Can I choose my airline with a Windsor Expedia vacation package?
Expedia has access to more than 550 partner airlines globally, so you certainly can. Simply choose your preferred air carrier and put together your ideal Windsor escape.
If I'm not able to travel, can I cancel my Windsor vacation package?
We totally get that life doesn't always go according to plan. If you've locked in a Windsor vacation package and have to amend or cancel it, we can help. We recommend taking a look at our Customer Service Portal first for information. But generally speaking, if you've taken out your package within 24 hours, you may be able to cancel and rebook for free. If it's more than 24 hours, your hotel, airline or car rental company may impose a charge.

Discover the most popular places to visit in Windsor

Montecasino

Montecasino

With shops, theaters and a bird park among the attractions, there’s fun for all the family during the day and night at this Tuscan-themed entertainment center.

Montecasino
Nelson Mandela Square

Nelson Mandela Square

Indulge in some retail therapy, dine in an open-air piazza and browse the stalls of an antique fair at this commercial and entertainment center.

Nelson Mandela Square
Gold Reef City which includes a city, a statue or sculpture and art

Gold Reef City Casino

Thrilling roller coasters, a 19th-century gold mine, cultural shows and a petting zoo provide entertainment for all ages at this popular theme park.

Gold Reef City Casino

Things to do

Johannesburg city

Half-Day Johannesburg City Tour with Pickup

CA $138
per adult
Half-Day Johannesburg City Tour with Pickup
Johannesburg Full-Day Tou

Johannesburg Full-Day Tour(Soweto/Jo-Burg & Apartheid Museum)

CA $189
per adult
100% of travellers recommend
Johannesburg Full-Day Tour(Soweto/Jo-Burg & Apartheid Museum)
Johannesburg, Apartheid Museum & Soweto

Johannesburg, Apartheid Museum & Soweto

CA $262
per adult
Johannesburg, Apartheid Museum & Soweto
See all activities in Johannesburg
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.